Acetyl chloride → 3'-Acetylaminomethylacetophenone

HRID 1734012Notes

Reaction equation

HRID 1734012 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.[C:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][NH2:13])(=[O:8])[CH3:7].C(N(CC)CC)C>ClCCl>[C:1]([NH:13][CH2:12][C:11]1[CH:10]=[C:9]([C:6](=[O:8])[CH3:7])[CH:16]=[CH:15][CH:14]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 247213721-[3-(aminomethyl)phenyl]ethan-1-one hydrochloride

Product 1

HCID 107977903'-AcetylaminomethylacetophenoneYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (2.5 g) was added slowly to a suspension of 3-acetylbenzylamine hydrochloride (5.0 g) and triethylamine (6.0 g) in dichloromethane (50 ml) with cooling on an ice-water bath. The mixture was stirred at room temperature for 10 hours. The solvent was removed under reduced pressure. The residue was dissolved in water (100 ml). The solution was alkalified with an aqueous potassium carbonate solution. The mixture was extracted with ethyl acetate (150 ml). The solution was dried with magnesium sulfate. The solvent was removed under reduced pressure to afford 3'-acetylaminomethylacetophenone (3.2 g) (oil).

Workup

  1. temperaturewith cooling on an ice-water bath
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in water (100 ml)
  4. extractionThe mixture was extracted with ethyl acetate (150 ml)
  5. dry with materialThe solution was dried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2db5fdd751924e1eb61013a002d6db61
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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